Richard Sanders recalls the exploits of Bartholomew Roberts, a swashbuckling 18th-century buccaneer to match Johnny Depp — except that he drank tea, and was probably gay

The Pirates of the Caribbean films, the third of which has just been released, have revived the age-old interest in all things piratical. But the average Victorian schoolboy would probably have choked on his porridge if he’d known the real nature of the men whose adventures he so avidly devoured.

If anyone deserves the title ‘the real pirate of the Caribbean’ it was the Welshman Bartholomew Roberts, who captured an astonishing 400 ships in a brief two-and-a-half-year career between 1719 and 1722 — a figure that dwarfs that of any of his contemporaries. Roberts was living proof that reality is always far, far more intriguing than fiction. He drank tea rather than rum. He organised his ships along strictly democratic, egalitarian lines. A third of his men were black. And he was probably gay.

Born to a farming family in Pembrokeshire, South Wales, in 1682, Roberts was captured by pirates while working as mate aboard a slaver off West Africa. Conditions aboard the slavers were almost as bad for the crew as they were for the cargo (their death rate was actually higher), and most were more than happy to be recruited into pirate crews. But Roberts was an exception. It’s likely he’d been raised a Baptist, and there was an austere, slightly puritanical streak to his personality. He felt a visceral revulsion at the drunken anarchy of the men looting his ship and begged to be released. But men like Roberts, who could read and write — and therefore navigate — were always in short supply on pirate ships and he was forced aboard.

Roberts was quickly seduced by pirate life. Compared with the harshness of life aboard the slavers, it was an existence of almost unimaginable ease and luxury. There wasn’t even much fighting, since the mere sight of the black flag was usually enough to send their victims scurrying to surrender. Roberts’s forceful, charismatic personality quickly impressed itself on the crew — so much so that when the pirate captain was killed in battle just six weeks later, Roberts was elected to replace him. He accepted command with the memorable words, ‘I have dipped my hands in muddy water and, if a pirate I must be, ’tis better being a commander than a common man.’

All pirate ships were governed by a set of rules known as ‘articles’. Those aboard Roberts’s ship have survived and clearly show the stamp of his puritanical personality. ‘No person to game at cards or dice for money,’ read article III. Article VI banned women aboard and stipulated that ‘any man found seducing’ a woman and ‘carrying her to sea disguised’ was to ‘suffer death’. Intriguingly, boys were also banned. Article XI stipulated that the ship’s musicians should have a day off on Sundays — a rare example of pirates respecting the Sabbath. Lights were to be out by eight in the evening, and the men were under strict instructions to keep their ‘pistols and cutlass clean and fit for action’.

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It was Roberts’s ability to harness the manic energies of his men to his own disciplined personality that set him apart from other pirate captains of the age. But his style of leadership created endless tensions. Pirate ships were floating republics. Not just the captain but all other officers were elected. Booty was divided between the whole crew with the captain’s share only twice that of a common man. Most pirates had escaped the tyranny of the merchant navy and it was the promise of freedom, above all, that drew them to life beneath the black flag. For many this meant freedom to drink themselves to oblivion, and the central drama of Roberts’s life would be the struggle of a sober, intelligent man to rein in the inherent anarchy of pirate life.

But Roberts’s success helped glue his crew — which at one point numbered more than 350 men — together. Through 1719 and 1720 they ravaged shipping along the entire eastern seaboard of the New World, from Brazil to Newfoundland. By the spring of 1720 they had brought all trade in the eastern Caribbean to a halt, and Roberts’s reputation as the greatest pirate of the age was firmly established.

The pirates Roberts gathered around him in some ways conformed to our stereotype, in some ways not. They really did dress in jewellery, white silk shirts and fine, embroidered waistcoats, like children let loose in a costume cupboard — 18th-century bling, conveying the unmistakable message to common seamen that crime paid.

There was also a smattering of wooden legs and eye patches. Pirates operated complex systems of injury insurance, and it was common practice to retain invalids in non-combatant roles. Like Long John Silver in Treasure Island, many ended up as ships’ cooks. Parrots were also popular pets, and those that could talk were valued particularly highly.

Roberts flew a black flag, although the designs he used were more complex than the conventional skull and crossbones. One showed Roberts himself standing astride two skulls representing ‘A Martinican’s Head’ and ‘A Barbadian’s Head’ — two islands he had particular hostility towards. Another showed a figure brandishing a flaming sword at a skeleton, ‘intimating a defiance of death itself’.

Neither Roberts nor any other pirate of this era ever made victims walk the plank. In fact, it’s remarkable how few people Roberts and his men killed. Of the 400 merchant ships they captured, just two put up a fight. Other than in battle, they never killed a single passenger or crew member from any of their prizes.

A third of Roberts’s men were black. Lest we are tempted to see pirate ships as politically correct utopias, it should be pointed out that most were probably slaves rather than fully fledged pirates. But they were trusted to bear arms, they did the work of skilled sailors, and they were among the most loyal members of the crew. It was no life for the squeamish, but for slaves in the early 18th century, this was probably about as good as it got. When finally captured, many showed themselves eager to escape and to return to a life of piracy.

Roberts, like most pirates, was unmarried. The Buccaneers, who had pioneered piracy in the Caribbean in the 17th century, lived in male couples. They pooled everything they possessed and referred to their partner as their ‘matelot’. The Buccaneers’ fiercely misogynistic culture was bequeathed to pirates of Roberts’s day, and it’s likely there were strong homoerotic undercurrents aboard Roberts’s ships. On the rare occasions his men did manage to hunt down pirate-friendly brothels they indulged themselves with wild excess. But there is no record of Roberts himself ever partaking in these pleasures. And during his final rampage down the coast of West Africa in late 1721 he developed an intensely emotional relationship with his young surgeon, George Wilson. The two men were ‘intimate’, according to witnesses, and even pledged a mutual suicide pact, swearing to ‘blow up and go to hell together’ rather than be captured. The strange sexual ambiguity that Johnny Depp brings to the lead role in Pirates of the Caribbean is probably the most accurate element in the entire film.

By this time Roberts was living on borrowed time. The slave trade had always been the principle focus of his activity, providing both the bulk of his prizes and the bulk of his crew, and an angry coalition of slave traders and plantation owners was clamouring for action against him.

Roberts was finally cornered at Cape Lopez in modern Gabon on 10 February  1722 by HMS Swallow, a 50-gun man-of-war. The pirates had taken a prize the day before and, having raided
the liquor store, most of the men were either drunk or nursing fierce hangovers — the scenario Roberts had always dreaded. Trapped against the headland, Roberts knew he was facing almost certain death. But he was determined to go out in style and dressed in ‘a rich crimson damask waistcoat and breeches, a red feather in his hat, a gold chain round his neck, with a diamond cross hanging to it’. In an apocalyptic final battle, fought in a raging thunderstorm, Roberts was killed, his throat ripped out by grapeshot as his men floundered drunkenly about the deck.

The defeat of Roberts and his men proved a turning-point in the history of the Atlantic. Within four years pirates had been swept from the seas altogether — and the number of slaves being shipped to the New World had increased dramatically, from 24,780 in 1720 to 47,030 in 1725. Piracy had been the thorn in the side of the fabulously lucrative triangular trade between Britain, Africa and the Americas. Its destruction helped create a world safe for slavery.

Richard Sanders’s ‘If a Pirate I Must Be…: The True Story of Bartholomew Roberts, King of the Caribbean’ is published by Aurum Press, £14.99.

This article first appeared in the print edition of The Spectator magazine, dated